Real Estate Investing for Cash Flow with Kevin Bupp

Chay Lapin is a real estate investment and 1031 exchange expert.

Chay is a leader and specialist within the 1031 DST and real estate offerings market. In this role, he offers insight to clients nationwide concerning multifamily and commercial real estate, DST, TIC, and fractional NNN Properties. Chay has also sponsored and co-sponsored the syndication of over two million square feet of DST properties in the multifamily, net lease, industrial, and office sectors and invested in and operated multiple net lease asset residential properties throughout the United States.

As the president of Kay Properties and Investments, a national Delaware Statutory Trust investment firm, Chay and his team provide their clients with access to the marketplace of DSTs from over 25 different sponsor companies, custom DSTs, independent advice on DST sponsor companies, full due diligence and vetting on DST and a DST secondary market and so much more. 

Prior, Chay was a four-time Academic All-American water polo athlete breaking records and receiving athletic awards at UCLA. As a top-ranked water polo athlete, Chay represented the United States in the 2012 London Olympic Games on the U.S. Men's National Water Polo Team.


"You're ultimately a passive investor, that's become very popular over the last decade, and then very popular with the acceptance that we are not a crowdfunding site but the whole crowdfunding world and the big companies getting involved in venture capital has allowed people to get comfortable with the passive investing." 

"In the DST's you can also do a cash investment into them. It's not just for 1031 exchange funds... So you do a cash investment today, there's that liquidity event, you can have an option with the current tax law to do a 1031 exchange."

"And that's the biggest difference between the DST structure and your typical GP structure or other funds is there's no waterfall split with the trustee; 100% of the upside goes to the investors, but the sponsor, the trustee, gets a disposition fee."


03:05 - Chay gives us insight into his background and education being a former Olympian, and how he got started in the real estate world.

06:42 -Chay tells us more about his internship experience.

08:08 - Chay tells us what a DST is and what role they play in real estate investment.

11:08 - Chay breaks down the DST structure. 

12:45 - Chay lists out the investor profiles that he typically works with as a 1031 exchange expert.

16:54 - Chay tells us more about the technicalities of being a beneficial owner. 

20:33 - What are some of the profiles of these properties in the DST world?

21:50 - Chay speaks about Kay's Secondary Market and options for people who need to quickly get liquidity in an illiquidity market.

24:10 - Talk about leverage and debt on DST properties.

Guest Website:

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Direct download: 329_Chay_Lapin_final_2.mp3
Category:general -- posted at: 1:00am EDT

Bill Ham a is real estate investment expert. 

Bill is the Chief Operating Officer and the driving force behind Broadwell Property Group. He has upwards of 20 years’ experience in the Real Estate investment world with a proven track record of identifying, acquiring, operating, and divesting large footprint Multifamily Housing. 


“The cap rate compression is too great at the moment. We are looking for a good deal like everyone else and we’re going to sit tight until we find one.” 

“One of the biggest mistakes I’m seeing people do right now is to really just buy into this ‘the rent is below market’ conversation. I am strongly cautioning everyone against that. What I’m seeing are the people that are basically mathematically looking at a deal and saying this is not a good deal mathematically speaking, but that’s okay because I can raise the rent and as soon as I raise the rent this will be a good deal.” 


1:27- Bill talks about his background and how he got into real estate 

5:56- Bill gives his opinion if things are a little too frothy right now and if he’s concerned that something may happen to impact pricing 

12:00- Bill talks about core cycles and where they pertain to 

14:20- Bill shares his investment strategy in the ‘COVID world’ 

17:05- Bill talks about some tactics that he wrote about in his book 

23:25- Bill talks about what he’s doing at this point in time to prepare for a potential future recession  

26:59- Bill shares his most challenging deal and what he learned from it 

Guest Website: 

Direct download: Bill_Ham_Edited.mp3
Category:general -- posted at: 12:00am EDT

Sterling Anderson is a real estate investor. 

Sterling is the President & CEO of Red Oak Development (Formerly Sterling Capital Investments), a Real Estate Development/Investment company based in Omaha, NE. The company invests in and develops single-family, Multifamily, and Hotel properties  


“It starts with the parent company. It starts with having to adhere to what they feel. You can have any idea in the world that you want, but if it’s not approved by AHG or Hilton or Radisson, then that’s an uphill battle that you’re facing.” 

“You always explain to your investors that there is a risk of you not receiving your capital back.” 

“I’d rather raise too much for deals and have to give some back than not raise enough.” 


2:04- Sterling talks about his background and how he got into the real estate space 

7:01- Sterling talks about where he finds distressed hotel sellers and pandemic pricing 

13:04- Sterling gives stats on what he's planning for his hotels and what he’s hoping for  

17:43- Sterling talks about hotel conversion to multi-family 

19:10- Sterling shares what markets he is excited about 

25:50- Sterling talks about day-to-day management with his hotels and how he avoids losing money with it 

30:06- Sterling talks about being with a flag and if it brings buying power 

33:11- Sterling shares his most challenging deal and what he learned from it 

Guest Website: 


Direct download: Sterling_Anderson_Edited.mp3
Category:general -- posted at: 12:00am EDT

Jill DeWit & Steven Butala are real estate and raw land experts. 

Since 1999, Jill and Steve have completed the acquisition and sale of more than 16,000 properties without incurring leverage or debt and continue to purchase property daily for immediate resale. 


“The seller just doesn’t want it anymore. They are tired of getting the tax bills. They’re in a situation and need cash right now. They inherited it and didn’t even know they had it. There are all kinds of situations and they just don’t know what to do.” 

“I love that we can buy and sell property all over the country and I don’t have to be there. We have members all over the world that are doing this very successfully.” 


2:25- Jill and Steve talk about how they got into the real estate space and how they ended up in land investments 

10:00- Jill and Steve share how they come up with the land value and what formula is used 

17:16- Jill and Steve talk about their program and the kind of results you can expect from it 

21:07- Jill and Steve talk about who the buyer typically is on the back end 

29:49- Jill and Steve talk about the due diligence they do on their properties prior to buying 

32:17- Jill and Steve share their most challenging deal and what they learned from it 

Guest Website: 


Direct download: Jill_DeWit_and_Steve_Butala_Edited.mp3
Category:general -- posted at: 12:00am EDT

Vince Guzzo is a businessman, entrepreneur, and philanthropist,  

Vince is a Canadian entrepreneur who currently serves as CEO of Guzzo Cinemas, Guzzo Construction inc., Guzzo Medical, and Guzzo Hospitality. 

Vince received national attention in 2018 when he joined the cast of the CBC Television business reality shows Dragons' Den as one of the investors. Additionally, Vince’s group is the largest movie operator in Quebec, with 141 screens and 10 locations, and the third-largest in Canada.  


“Movie theatres have been competing with some form of in-home entertainment for about 120 years. At the end of the day, content is king. What does that content cost you? What is your talent in storytelling?” 

“The deals that I did do, whatever mistake I made, I managed to turn the mistake into a learning lesson and at the end of the day, I don’t regret the bad deals. It’s the ones I didn’t do that I regret.” 


1:32- Vince talks about his background and how he landed in the cinema space 

9:15- Vince talks about if a business owner or idea itself is more important 

11:46- Vince shares how COVID has impacted the cinema business 

14:47- Vince talks about design changes prompted by COVID 

19:08- Vince shares if cinemas have a plan to get people comfortable and excited for theatres again 

26:27- Vince talks about how malls are doing in Canada and how that impacts cinemas 

33:00- Vince talks about how streaming services have impacted the cinema industry 

44:28- Vince shares his most challenging deal and what he learned from it 

Guest Website: 


Direct download: Vince_Guzzo_Edited.mp3
Category:general -- posted at: 12:00am EDT